# US 2014/0151094 A1 · Active ester resin, method for producing the same, thermosetting resin composition, cured product of the thermosetting resin composition, semiconductor encapsulating material, pre-preg, circuit board, and build-up film > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0151094 A1 - Document ID: US20140151094A1 - Status: Published application - Kind: A1 - Application number: 13/824,821 - Filed: 2012-05-25 - Published: 2014-06-05 - Earliest claimed: 2011-05-27 - Assignees: DIC Corporation - Inventors: Kan Takeuchi; Etsuko Suzuki; Kunihiro Morinaga; Kazuo Arita - Web page: https://patentgrep.com/patent/US20140151094A1 ## CPC - H05K 3/00: Apparatus or processes for manufacturing printed circuits - C08G 8/32: by organic acids or derivatives thereof, e.g. fatty oils - C08G 59/4223: {aromatic} - C08G 63/133: Hydroxy compounds containing aromatic rings - C08G 63/605: {the hydroxy and carboxylic groups being bound to aromatic rings} - C08J 5/244: {using glass fibres} - C09D 161/14: Modified phenol-aldehyde condensates - C09D 167/00: Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain (based on polyester-amides C09D177/12; based on polyester-imides C09D179/08); Coating compositions based on derivatives of such polymers - H05K 1/0353: {consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement} - H10W 74/40: characterised by their materials - Y10T 428/2915: including textile, cloth or fabric - Y10T 428/31529: Next to metal - Y10T 442/2475: Coating or impregnation is electrical insulation-providing, -improving, or -increasing, or conductivity-reducing - H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - H10W: GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10 - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract A low dielectric constant, a low dielectric loss tangent, and heat resistance are achieved. An active ester resin that has a resin structure produced by reacting a polyfunctional phenolic compound (a1) with a monofunctional aromatic carboxylic acid or its chloride (a2) and an aromatic dicarboxylic acid or its chloride (a3). The polyfunctional phenolic compound (a1) is represented by structural formula (1) below: (where Ar represents a benzene ring, a naphthalene ring, a benzene ring nuclear-substituted by an alkyl group having 1 to 4 carbon atoms, or a naphthalene ring nuclear-substituted by an alkyl group having 1 to 4 carbon atoms, X represents a methylene group, a divalent cyclic aliphatic hydrocarbon group, a phenylene dimethylene group, or a biphenylene-dimethylene group, and n represents the number of repeating units and the average thereof is in a range of 0.5 to 10). ## Claims ### Claim 1 A novel active ester resin comprising a resin structure produced by reacting a polyfunctional phenolic compound (a1) with a monofunctional aromatic carboxylic acid or its chloride (a2) and an aromatic dicarboxylic acid or its chloride (a3) in such a manner that an amount of the monofunctional aromatic carboxylic acid or its chloride (a2) is 0.46 to 0.95 moles and an amount of the aromatic dicarboxylic acid or its chloride (a3) is 0.27 to 0.025 moles per mole of phenolic hydroxyl groups of the polyfunctional phenolic compound (a1), the polyfunctional phenolic compound (a1) being represented by structural formula (1) below: (wherein Ar represents a benzene ring, a naphthalene ring, a benzene ring nuclear-substituted by an alkyl group having 1 to 4 carbon atoms, or a naphthalene ring nuclear-substituted by an alkyl group having 1 to 4 carbon atoms; X represents a methylene group, a divalent cyclic aliphatic hydrocarbon group, a phenylene dimethylene group, or a biphenylene-dimethylene group; and n represents the number of repeating units and an average thereof is in a range of 0.5 to 10). ### Claim 2 (depends on 1) The novel active ester resin according to claim 1, wherein a softening point is in a range of 70° C. to 140° C. ### Claim 3 (depends on 1) The novel active ester resin according to claim 1 that has a carbonyloxy structure in a proportion of 180 to 400 g/eq. ### Claim 4 A method for producing an active ester resin, the method comprising reacting a polyfunctional phenolic compound (a1) with a monofunctional aromatic carboxylic acid or its chloride (a2) and an aromatic dicarboxylic acid or its chloride (a3) in such a manner that an amount of the monofunctional aromatic carboxylic acid or its chloride (a2) is 0.46 to 0.95 moles and an amount of the aromatic dicarboxylic acid or its chloride (a3) is 0.27 to 0.025 moles per mole of phenolic hydroxyl groups of the polyfunctional phenolic compound (a1), the polyfunctional phenolic compound (a1) being represented by structural formula (1) below: (wherein Ar represents a benzene ring, a naphthalene ring, a benzene ring nuclear-substituted by an alkyl group having 1 to 4 carbon atoms, or a naphthalene ring nuclear-substituted by an alkyl group having 1 to 4 carbon atoms; X represents a methylene group, a divalent cyclic aliphatic hydrocarbon group, a phenylene dimethylene group, or a biphenylene-dimethylene group; and n represents the number of repeating units and an average thereof is in a range of 0.5 to 10). ### Claim 5 (depends on 4) The method for producing an active ester resin according to claim 4, wherein the polyfunctional phenolic compound (a1) is reacted with the monofunctional aromatic carboxylic acid or its chloride (a2) and the aromatic dicarboxylic acid or its chloride (a3) in the presence of an acid catalyst. ### Claim 6 A curable resin composition comprising an active ester resin (A) and an epoxy resin (B) as essential components, the active ester resin (A) having a resin structure produced by reacting a polyfunctional phenolic compound (a1) with a monofunctional aromatic carboxylic acid or its chloride (a2) and an aromatic dicarboxylic acid or its chloride (a3) in such a manner that an amount of the monofunctional aromatic carboxylic acid or its chloride (a2) is 0.46 to 0.95 moles and an amount of the aromatic dicarboxylic acid or its chloride (a3) is 0.27 to 0.025 moles per mole of phenolic hydroxyl groups of the polyfunctional phenolic compound (a1), the polyfunctional phenolic compound (a1) being represented by structural formula (1) below: (wherein Ar represents a benzene ring, a naphthalene ring, a benzene ring nuclear-substituted by an alkyl group having 1 to 4 carbon atoms, or a naphthalene ring nuclear-substituted by an alkyl group having 1 to 4 carbon atoms; X represents a methylene group, a divalent cyclic aliphatic hydrocarbon group, a phenylene dimethylene group, or a biphenylene-dimethylene group; and n represents the number of repeating units and an average thereof is in a range of 0.5 to 10). ### Claim 7 (depends on 6) The curable resin composition according to claim 6, wherein the active ester resin (A) has a softening point in a range of 70° C. to 140° C. ### Claim 8 (depends on 6) The curable resin composition according to claim 6, wherein the active ester resin (A) has a carbonyloxy structure in a proportion of 180 to 400 g/eq. ### Claim 9 (depends on 6) A cured product produced by curing the curable resin composition according to claim 6. ### Claim 10 (depends on 6) A semiconductor encapsulating material comprising a thermosetting resin composition containing an inorganic filler (C) in a proportion of 70% to 95% by mass in the composition in addition to the active ester resin (A) and the epoxy resin (B) of the curable resin composition according to claim 6. ### Claim 11 (depends on 6) A pre-preg produced by impregnating a reinforcement substrate with the curable resin composition according to claim 6, the curable resin composition being diluted with an organic solvent, and semi-curing the resulting impregnated substrate. ### Claim 12 (depends on 6) A circuit board produced by diluting the curable resin composition according to claim 6 with an organic solvent to prepare a varnish, shaping the varnish into a plate, and molding the plate and a copper foil under heat and pressure. ### Claim 13 (depends on 6) A build-up film produced by applying the curable resin composition according to claim 6 to a base film and drying the film, the curable resin composition being diluted with an organic solvent. ### Claim 14 (depends on 7) A cured product produced by curing the curable resin composition according to claim 7. ### Claim 15 (depends on 8) A cured product produced by curing the curable resin composition according to claim 8. ### Claim 16 (depends on 7) A semiconductor encapsulating material comprising a thermosetting resin composition containing an inorganic filler (C) in a proportion of 70% to 95% by mass in the composition in addition to the active ester resin (A) and the epoxy resin (B) of the curable resin composition according to claim 7. ### Claim 17 (depends on 8) A semiconductor encapsulating material comprising a thermosetting resin composition containing an inorganic filler (C) in a proportion of 70% to 95% by mass in the composition in addition to the active ester resin (A) and the epoxy resin (B) of the curable resin composition according to claim 8. ### Claim 18 (depends on 7) A pre-preg produced by impregnating a reinforcement substrate with the curable resin composition according to claim 7, the curable resin composition being diluted with an organic solvent, and semi-curing the resulting impregnated substrate. ### Claim 19 (depends on 8) A pre-preg produced by impregnating a reinforcement substrate with the curable resin composition according to claim 8, the curable resin composition being diluted with an organic solvent, and semi-curing the resulting impregnated substrate. ### Claim 20 (depends on 7) A circuit board produced by diluting the curable resin composition according to claim 7 with an organic solvent to prepare a varnish, shaping the varnish into a plate, and molding the plate and a copper foil under heat and pressure. ### Claim 21 (depends on 8) A circuit board produced by diluting the curable resin composition according to claim 8 with an organic solvent to prepare a varnish, shaping the varnish into a plate, and molding the plate and a copper foil under heat and pressure. ### Claim 22 (depends on 7) A build-up film produced by applying the curable resin composition according to claim 7 to a base film and drying the film, the curable resin composition being diluted with an organic solvent. ### Claim 23 (depends on 8) A build-up film produced by applying the curable resin composition according to claim 8 to a base film and drying the film, the curable resin composition being diluted with an organic solvent.